N-Benzyl-D-proline ethyl ester

Base Information

• Chemical Name: N-Benzyl-D-proline ethyl ester
• CAS No.: 172478-10-3
• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 233.31
• Hs Code.: 2933990090
• European Community (EC) Number: 624-346-2
• DSSTox Substance ID: DTXSID80350813
• Nikkaji Number: J725.670A
• Wikidata: Q82126914
• Mol file: 172478-10-3.mol

Synonyms:N-Benzyl-D-proline ethyl ester;172478-10-3;(R)-Ethyl 1-benzylpyrrolidine-2-carboxylate;ethyl (2R)-1-benzylpyrrolidine-2-carboxylate;(R)-1-BENZYL-PYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER;Ethyl 1-benzylpyrrolidine-2-carboxylate;SCHEMBL4937902;1-Benzyl-D-proline ethyl ester;DTXSID80350813;MFCD00134579;AKOS015910521;N-Benzyl-D-proline ethyl ester, 98%;D-Proline,1-(phenylmethyl)-,ethylester;A811417;J-010824

Chemical Property of N-Benzyl-D-proline ethyl ester

Chemical Property:

• Vapor Pressure: 0.000662mmHg at 25°C
• Refractive Index: n20/D 1.511(lit.)
• Boiling Point: 308.9 °C at 760 mmHg
• Flash Point: 107.4 °C
• PSA: 29.54000
• Density: 1.099 g/cm³
• LogP: 2.15200
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 233.141578849
• Heavy Atom Count: 17
• Complexity: 249

Purity/Quality:

99%min ^*data from raw suppliers

(R)-Ethyl1-benzylpyrrolidine-2-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CCCN1CC2=CC=CC=C2
• Isomeric SMILES: CCOC(=O)[C@H]1CCCN1CC2=CC=CC=C2

Technology Process of N-Benzyl-D-proline ethyl ester

There total 11 articles about N-Benzyl-D-proline ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 67.0%

diazoacetic acid ethyl ester (623-73-4) + N-benzyl azetidine (7730-39-4) → 1-Benzyl-pyrrolidin-2-carbonsaeure-ethylester (60251-42-5,172478-10-3)

Guidance literature:

With copper; In toluene; regioselective reaction; Reflux; Inert atmosphere;

DOI:10.1021/jo9001323

Reference yield: 44.0%

methanol (67-56-1) + dimethyl 2-{[N2-(1-benzylpyrrolidin-2-yl)carbonyl]hydrazino}-3-cyanobut-2-enedioate → dimethyl 3-amino-1H-pyrazole-4,5-dicarboxylate + N-benzyl-L-proline ethyl ester (955-40-8,172478-10-3)

Guidance literature:

In methanol; at 20 ℃;

DOI:10.3987/COM-12-S(N)16

Reference yield: 40.0%

C26H30NO4P (172223-90-4) → 1-Benzyl-pyrrolidin-2-carbonsaeure-ethylester (60251-42-5,172478-10-3) + 5-{[1-Phenyl-meth-(E)-ylidene]-amino}-pentanoic acid ethyl ester

Guidance literature:

With lithium diisopropyl amide;

DOI:10.1016/0040-4039(95)01567-2

upstream raw materials:

C₂₆H₃₀NO₄P

ethyl 5-bromovalerate

N-benzyl hydroxylalmine

5-(Benzyl-hydroxy-amino)-pentanoic acid ethyl ester

Downstream raw materials:

ethyl (2S)-pyrrolidine-2-carboxylate

Refernces

• 1、 Haraguchi, Ryosuke,Matsubara, Seijiro. "Catalytic asymmetric aldol-type reaction of zinc enolate equivalent of amides". supporting information. p. 3378 - 3380. Retrieved 2013/07/26.
• 2、 Mloston, Grzegorz,Pieczonka, Adam M.,Wroblewska, Aneta,Linden, Anthony,Heimgartner, Heinz. "Reactions of amines and hydrazides derived from L-proline with dialkyl dicyanofumarates". . p. 343 - 356. Retrieved 2013/08/15.